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Not a Newsletter

Not a Newsletter: December 2022

Welcome to the December edition of Not a Newsletter, a monthly, semi-comprehensive, Google Doc-based guide to sending better emails! I’m Dan, the founder of Inbox Collective, an email consultancy, and the former Director of Newsletters at The New Yorker and BuzzFeed. Every month, I update this doc with email news, tips, and ideas. Sign up here to be notified when the next edition goes live!

This month: Ask a Deliverability Expert is back and answering the question: Will switching ESPs improve deliverability for your newsletter? Plus, stories about when to use (or not use) double opt-in, and why you might not want to resend your emails to readers who didn’t open. And we’ll close with oddly-specific predictions for 2023.

Want to read a previous edition of Not a Newsletter? Find the full archive at this link.

-Dan 

(Email / LinkedIn)

A woman is on the phone with a man named Richard. She says: "We need to talk. I'll email you."
Aaron Bacall / The New Yorker

This Month in Email Headlines

New on inboxcollective.com

Ask a Deliverability Expert: Will Switching ESPs Improve Deliverability For My Newsletter?

Deliverability isn’t just about which ESPs you use, writes our deliverability expert, Yanna-Torry Aspraki. It’s also about you — what emails you send, who you send to, how often you send, and how you grow your audience.

If you do decide to make a switch, it’s critical to understand which party — you, or your ESP — has which responsibilities during the migration. The better you understand which best practices need to be implemented, the better the chance that you’ll leave those deliverability problems behind at your old ESP and give your audience every chance to receive your emails and engage with you moving forward.  Here’s Yanna-Torry’s advice if you’re thinking about switching.

Launching a Paid Newsletter Gave Me the Freedom to Say ‘No’

In March 2021, Chris LaTray — a Métis storyteller who writes the weekly newsletter “An Irritable Métis” — decided to turn on a paid option for his newsletter. Now, about 13 percent of his audience pays either $5 every month or $50 a year — even though nearly everything he writes in his newsletter is available to all readers, regardless of subscriber status.

And as Chris explains: “Opening up a paid option for ‘An Irritable Métis’ was without a doubt the most significant decision I’ve yet made in my writing career.” He’s now making his living as a full-time writer, and able to choose which projects he wants to work on, and which he wants to say “no” to. Here’s Chris’s story.

Digging Into ‘Dirt,’ a Digital Entertainment Newsletter

We’ve got lots of exciting things on tap for you on inboxcollective.com in 2023, but here’s a sneak peak at one new feature: FWD Progress. We’ll use it to spotlight newsletters innovating the form in one way or another (like content, monetization, or community), and explore the nuts and bolts of their strategy. To kick things off, Evelyn Crowley profiled Dirt, the cult digital entertainment newsletter that’s partly funded by sales of non-fungible tokens (NFTs).

I’ll admit: I don’t know much about the blockchain, but Dirt’s numbers are eye-opening: 18,000 subscribers, and $90,000 raised from NFT sales in 2021. And I love how Dirt is trying to include their members in their editorial process — they’re doing something worth paying attention to. Here’s how they’re building their newsletter strategy.

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For Your Reading / To-Do List

  • How do you move your email from the Promotions tab to the main inbox? The team at Westfield Creative surveyed 15 experts, and you’ll notice something among their answers: There isn’t a single deliverability hack in the mix. The best way to stay in the inbox is also the simplest: Be thoughtful about the emails you send your readers.
  • The team at Mailmodo put together an eBook with ideas for doing more with subject lines. I particularly liked reading about the test they ran for their own newsletter, which featured three different types of subject lines:
    • Curiosity-driven subject lines
    • Asking a question
    • Using a call to action
      • And then they collected feedback from readers about why they responded to each type of subject line. It’s worth a read!
  • There’s no *right* time to send a newsletter. But I did find this, from Aweber CEO Tom Kulzer, absolutely fascinating: Most newsletters are sent at the top of the hour… but there’s a lull that happens in the 10 minutes before then (minutes :50 through :59). Maybe you’ll want to adjust your send times accordingly.
  • Yes, the body of a newsletter is probably the most important part of your email, but you shouldn’t neglect the header and footer spaces. Email on Acid put together a nice guide for opportunities to get more out of your header.
  • Scaling CRM’s Drew Price wrote about why single opt-in is often the right choice for email marketers — as long as you’re taking a few other steps (like removing inactive readers, utilizing CAPTCHA or another authentication tool, or setting up a preferences center) alongside it.
  • And here’s a counterpoint, from Andrew Donovan’s Thanks For Unsubscribing newsletter: “Why I’m Turning On Double Opt-In For All My Clients.”
    • So who’s right? I’d argue that the right strategy involves a mix of both tactics. Drew is right that you need to be proactive in managing your lists, and Andrew is right that there are specific cases, like giveaways, where it makes sense to turn on double opt-in. (That’s something I recommend to my own clients.) 
  • I love seeing newsletter success stories from around the world. Here’s one from Finland, where Johanna Käkönen and Rami Nieminen of Finnish newsroom Turun Sanomat explained why newsletters have been such a valuable tool for retaining paying subscribers.
  • Some ESPs will recommend that you resend your newsletter to readers who don’t open it the first time. Tyler Denk, co-founder of Beehiiv, wrote about why he doesn’t recommend that tactic to users, and why it might negatively affect your open rate for future email sends.
    • My take on this: It’s OK to resend a newsletter, but do it sparingly, and only for high-value emails. If you’re sending out a huge announcement that needs to reach as many readers as possible, I’m fine with resending to non-openers. If you’re doing it to get a few hundred (or thousand) additional opens on a run-of-the-mill newsletter send, that’s probably not the best idea.
  • From the indie newsletter space:
  • It’s 2023 prediction season! (I’ve got mine at the very bottom of this Google Doc.) Here are 10 that Litmus collected from industry experts.
    • Cory Brown of the 99 Newsletter Project put together a really nice wishlist of newsletter trends he’d like to see in 2023. (Yes to “more newsletters sent from a real person and real email address”!)
    • Robin Sloan addressed a key trend for 2023: The big platforms of the past decade are becoming less and less relevant. So if that’s the case, what’s next for those of us who create content online? “A year of experimentation and invention,” Robin argues. Read the whole essay — like most stuff Robin writes, it’s great.
    • I wrote about something I’ve been saying to a lot of the indie newsletter writers I work with: Whatever you choose to do with your strategy in 2023, make it work for you.
  • And finally: I wanted to take a moment to acknowledge Grant Wahl, the American soccer writer who died while covering the World Cup. I didn’t personally know Grant, but I’d followed his work since his Sports Illustrated days. When he went independent, I started paying even closer attention. He had a podcast and contributed occasional freelance pieces for other outlets, but the majority of his original work appeared in his own newsletter, where he’d accrued thousands of paying subscribers. Over the past 18 months, when independent writers have asked me for a great example of a reporter-driven newsletters, Wahl’s was one of the first ones I shared. As Alex Hazlett and I wrote about Wahl’s newsletter back in August:

Great reporting doesn’t just have to be in politics or hard news. Fútbol with Grant Wahl, a newsletter primarily about American soccer by a former Sports Illustrated reporter, saw growth after Wahl traveled to cover every U.S. men’s World Cup qualifier. (He was the only English-language reporter to do so.) Exclusive reporting or storytelling often gets read and shared by that reporter’s audience — and, in turn, the sharing of those stories brings in new newsletter subscribers.

  • Building a paid subscription newsletter isn’t easy — it requires exceptional work. Wahl did exactly that, putting together magazine-style features and post-match recaps that set his work apart from the rest. I hope others will be inspired by the work he did — not just for excellence in reporting, but also as a model for building out a reporter-led subscription newsletter.

Stuff I Loved This Month

  • I helped audit a handful of independent news businesses as part of a LION/Google News Initiative program in 2022. Along with a few other auditors, I shared some thoughts on what these independent outlets can do to scale their businesses in the years ahead.
  • You’ll be unsurprised to find out that I absolutely loved this experiment: Demand Curve and Katelyn Bourgoin announced a new digital course, but instead of building a traditional landing page for it, they used… a Google Doc. Why? The combination of a limited number of seats available + seeing all the other people in the Google Doc created urgency for potential buyers. (And yes, this really worked! They sold out the first 50 seats for the course.)
  • Tracking the impact of your work — particularly at newsrooms that do big investigations — can be tricky. The Markup’s been using Airtable to track impact — and now they’ve released that Airtable to the public so you can use it, too.
  • I’m still stunned by this story about Phil O’Brien, a Brit living here in New York City who runs a news operation called W42St. He’s been building it since 2014, first as a print magazine, and now as a digital-only site with several excellent newsletters. He recently returned to the U.K. to get his visa renewed but had his application rejected. He was told his news operation, which employs several Americans, was “marginal.” I’m hoping the U.S. government will revisit Phil’s case and make the right choice — we need more news entrepreneurs like him!
    • Full transparency: I work with both The Markup and W42St. (Though I don’t think you need to be a client of Phil’s to be outraged about his story!)
  • My very first client, way back in 2019, was a site called Clean Plates, which writes about healthy eating and living. They’ve recently rolled out a cool new platform, Wellzy Perks, where members get access to impressive discounts and deals on brands in the health and wellness space. If your company’s interested in offering Wellzy Perks memberships to your employees, shoot me a note — happy to connect with Jared and the WP team!
  • WBEZ’s Curious City series has been so successful, it spun off a standalone company, Hearken, which now works with newsrooms around the world. The origin story of the series — and how they’ve evolved and improved it over the past decade —is fascinating.
  • And lastly: A decade ago, I met Tiffany Shackelford. I was a reporter, working in Springfield, Missouri, on a small news project. Tiffany saw something in that project and offered me the chance to speak at a big news conference she was putting on. It was the very first time I’d ever been invited to be a featured speaker at a conference. She was one of the people who helped open the door to get me to where I am today.
    • And there are literally hundreds of people in the news business who have a story like that about Tiffany. She went above and beyond, over and over again, to help the next generation of journalists.
    • Tiffany passed away in 2020 due to complications from COVID-19. But her family and friends have stepped up to create the Tiffany Shackelford Foundation, a new non-profit dedicated to opening more pathways in the media business for women and underrepresented groups. I hope you’ll consider supporting them in their mission.

And finally… 2023 Email Predictions!

It’s the end of the year, which means it’s the time when experts start making predictions about what will happen in the year ahead. I love hearing from experts about the trends they foresee arriving in the new year. But I do have one gripe with these predictions: They’re never quite specific enough! I call on my fellow experts to go further, to look into their crystal balls and truly help us understand what’s ahead.

But before we do that, let’s first look back on a few predictions of mine from last year:

✅ More organizations will add their personal story to newsletters + automations — I’m thrilled that this came true in 2022. So many orgs — from newsrooms to non-profits to eCommerce businesses — made an effort to sound more human in their emails this year. More of this in the year ahead, please!

✅ More newsletters will encourage a 1-to-1 conversation with your audience — I’ve long done this in Not a Newsletter — when you sign up for my newsletter, I ask you to reply and share a few things with me. It’s good to see more newsletters trying similar tactics: Asking questions, encouraging readers to take a poll, or making an effort to reply to each and every reader.

❌ More orgs will set up BIMI — This was a big miss for 2022. According to a September report from RedSift, only 51.2% of companies in the S&P 500 have a DMARC policy in place, and only 2.4% of them have applied for a Verified Mark Certificate to turn on BIMI. I’m shocked that these numbers are so low — more large orgs should look to set up DMARC and turn on BIMI in 2023.

❌ Wayne, a three-headed demon, will rise from the Earth’s molten core to terrorize the planet after an asteroid strikes Alberta, Canada — This was a rather bold prediction, and I’m thrilled to have been wrong! (Wayne would’ve been very bad news for all of us in the email community, and also humankind on the whole.)

But that’s the risk you take when you make big, oddly-specific predictions for the year ahead! Some are right, but many will be wrong. I’ll try to do better for 2023. 

And with that in mind: Here’s what I’m predicting for the new year:

▶ I think we’ll see some consolidation in the indie newsletter space — Going it alone as an independent subscription newsletter is tough. There have been a handful of big winners in this space, but a lot of folks are stuck in a weird bit of limbo: They’re making enough money to be excited about the future of subscriptions, but not enough to work full time on their subscription newsletter. I think we’ll see many form partnerships and create new publications (think: Puck, Workweek, Every), pooling their subscriptions together to create a more sustainable business.

▶ I think we’ll see more newsletters lean into surveys — Surveys are a massive opportunity for any newsletter (see: The Financial Times and the 78,000 replies they got on a survey), and more newsletters will make regular surveys a key part of their newsletter strategy. If you’re not making time to listen to your readers, you’re probably not building something that truly works for them. 

▶ I think you’re going to attend at least two talks next year from a newsletter expert who says it’s time to start personalizing your newsletters — And despite the exciting tone of those keynotes, I don’t think 2023 is the year it will happen.  Most newsletter businesses aren’t that close to being able to do much with personalization. I think we’re a year away from being a year away from personalization coming to newsletters.

▶ I think you’re going to make an embarrassing purchase based on an email offer — It’s going to be in March — I’m thinking March 7. One of those days where you thought things were warming up, but then the weather suddenly flipped back to mid-winter. You’re not going to want to leave the house. And then: Domino’s Pizza shows up in your inbox, reminding you that your reward points are about to expire. You swore that you were better than Domino’s — you went to Naples last year! You call it pizza margherita now! And yet: Those points! They’re expiring! The email even has one of those countdown clocks, reminding you of the urgency of the matter. You’ll order two medium pizzas, with mushroom and olives, and just before entering your credit card information, you’ll return to your cart to add cheesy breadsticks. You will eat your pizza and cheesy breadsticks quietly on the couch. You will tell no one. You will swear that this is the last time. You will get an email in mid-November reminding you that your reward points are expiring, and you will repeat the process again.

▶ I think the U.S. will win the 2023 Women’s World Cup, and I think Trinity Rodman will win the Golden Boot as the top goalscorer in the tournament — This has nothing to do with email or marketing — I just want to put it on the record now. (I’ve officially got World Cup fever, and I’m ready for more in the new year!)

▶ I think you’re going to start to see AMP for Email in more newsletters — You won’t see huge interactives or any of the big ideas that we were promised with AMP for Email. What you will see will be small and practical: Forms to offer feedback. One-click polls. Buttons to add events to your calendar. (And, yes, the ability to purchase a Domino’s Pizza without leaving the inbox.) This is the kind of stuff that makes the inbox just a little bit better. Maybe it’s what we should’ve been focusing on all along with AMP.

▶ And finally: Google Doc-inspired animals will be making a comeback to this space — They’re designed, they’re drawn, and they’re ready. Watch this space in January. I’ve got some fast facts about owls to share.

Here's a decorative image of three animals: An owl, a flamingo, and a seahorse

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By Dan Oshinsky

Dan runs Inbox Collective, a consultancy that helps news organizations, non-profits, and independent operators get the most out of email. He specializes in helping others build loyal audiences via email and then converting that audience into subscribers, members, or donors.

He previously created Not a Newsletter, a monthly briefing with news, tips, and ideas about how to send better email, and worked as the Director of Newsletters at both The New Yorker and BuzzFeed.

He’s been a featured speaker at events like Litmus Live in Boston, Email Summit DK in Odense, and the Email Marketing Summit in Brisbane. He’s also been widely quoted on email strategies, including in publications like The Washington Post, Fortune, and Digiday.